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3S-(+)-3,7-Dimethyl-1,5,7-octatriene-3-ol in the
Essential Oil of Black Tea
To cite this article: Yoichi Nakatani, Sumiko Sato & Tei Yamanishi (1969) 3S-(+)-3,7-
Dimethyl-1,5,7-octatriene-3-ol in the Essential Oil of Black Tea, Agricultural and Biological
Chemistry, 33:6, 967-968, DOI: 10.1080/00021369.1969.10859406
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,.,--, ... --- -
.s" 70 :'
"'"' 60
''
~ 50
E
40
:!
~,J
0~ 30
20
10
4000 3600 3200 2800 2400 2000 1900 1800 1700 1600 1500 1400 1300 1200 1100 1000 900 800 700 600
1
\\'a\'e numher I em )
FIG. 1. Infrared Spectra of Natural and Synthetic 3R-(- )-3, 7-dimethyl-1 ,5, 7-octatriene-3-ol (neat film).
Full line: Natural one
Broken line: Synthetic one
* Experimental parameters of GLC were as fol- 3) T. Yamanishi, Eiyo to Shokuryo, 21, 227 (1968).
lows; 4) S. Muraki, The 11th Symposium on the Chemis-
Column: 3 mm X 187 em stainless steel, try of Terpenes, Essential Oils and Aromatics, Matsu-
Carbowax 20M 2396 on Chromosorb W yama, Japan, Oct., 1967, p. 30.
60/80, 5) G. Ohloff und E. Klein, Tetrahedron, 18, 37 (1962).
Carrier gas: Helium, 20 mlfmin, 6) R. S. Mulliken, ]. Chern. Phys., 7, 121 (1939).
Column Temp.: 15ooc. * After this article was accepted, T. Yoshida et al.
1) T. Yamanis~i, A. Kobayashi, H. Nakamura, reported the determination of the configuration of
A. Uchika, S. Mon, K. Osawa and S. Sasakura, Agr. (- )-trans-Hotrienoi: T. Yoshida, S. Muraki, H. Kawa-
Biol. Chern., 32, 379 (1968). mura and A. Komatsu, Agr. Biol. Chern., 33, 343
2) T. Yamanishi, T. Kiribu~hi, M. Sakai, N. (1969).
Fujita, Y. Ikeda and K. Sasa, tbtd., 27, 193 (1963).
968 Y. NAKATANI, S. SATO and T. YAMANISHI
Nss+n+n+n
B~ ~BrBr~
I
(R -configuration) (R -configuration l
6'"/
~Oil
nOCOCH,
~ --:K:-:'O'""H----'""
II
(R- configuration) (R- configuration) (R- configuration)
HO-Leaf Oil tion (!-form; .{~'.?xH 230 mp, log s4.4 and d-form:
A:;;~: 230 mp, log s4.3) of these compounds in-
dicate that their conjugated double bonds exist
in the S-trans conformation.
It is very interesting that both linalool and
(3R)-(-) (3R)-(-) 3, 7-dimethyl-1 ,5, 7-octatriene-3-ol in black tea
have 3S-configuration, while those in Ho-leaf
Black Tea
have 3R-configuration. This fact as well as the